Tetrahydrofuran → 3-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)propanol

HRID 2294367Notes

Reaction equation

HRID 2294367 reaction equation
[O:1]([CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH2:15][CH2:16][C:17](OCC)=[O:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Li+]>CO>[O:1]([CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21474742Ethyl 3-(5-phenoxymethyl-2-oxooxazolidin-3-yl)propionate

Product 1

HCID 214747813-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)propanolYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Preparation 5(a) was repeated, except that 1.64 g of ethyl 3-(5-phenoxymethyl-2-oxooxazolidin-3-yl)propionate (prepared as described in Preparation 113), 15 ml of anhydrous tetrahydrofuran, 244 mg of lithium borohydride and 179 mg of anhydrous methanol were used, to give 1.41 g of the title compound having an Rf value of 0.28 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-3726d807fa8a46a5b5f47125a9b808e3
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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